Potassium tert-butoxide → 7-Chloro-3,5-dihydrobenzo[e][1,4]oxazepin-2(1H)-one

HRID 72174Notes

Reaction equation

HRID 72174 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[CH2:13][OH:14])=[O:4].CC(C)([O-])C.[K+]>CC(O)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:3](=[O:4])[CH2:2][O:14][CH2:13][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 866797092-Bromo-N-(4-chloro-2-(hydroxymethyl)phenyl)acetamide

Product 1

HCID 840481997-Chloro-3,5-dihydrobenzo[e][1,4]oxazepin-2(1H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-bromo-N-(4-chloro-2-(hydroxymethyl)phenyl)acetamide (3.60 g, 12.9 mmol) in 2-propanol (129 ml) was added in small portions potassium tert-butoxide (3.77 g, 33.6 mmol) at 0-5° C. The reaction mixture was stirred for 90 minutes and subsequently poured on ice/water (500 ml). The precipitate was collected by filtration and washed with water. Residual water was removed by consecutive evaporation with two 50-ml portions of toluene to give the title compound (2.34 g, 92%) as light yellow solid. MS m/e: 196 ([M−H]−).

Workup

  1. additionsubsequently poured on ice/water (500 ml)
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customResidual water was removed by consecutive evaporation with two 50-ml portions of toluene

Sources & evidence

ORD record
ord-cc594ae9adbe4d44a9b6738d7b08aeef
Source dataset
uspto-grants-2014_09
Patent number
US08828989B2

Reaction notes

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